Caged and Loving it
by Little-Dark-Scopio
Summary: Sydney meets a boy that is eager for a Mistress to submit too and by chance one such blossoming Mistress walked in on him, the question is does Sydney have what it takes? Max trying to impress a girl had an accident and later angered said girl and he would do just about anything to enter her good graces. Will he crumble under the pressure?
1. Chapter 1

**Disclaimer**

Neither one of us have any rights to Sydney to the Max. We have not met the actors nor privy to their sexuality. We do own this story.

**Author Note**

Sydney part is written by L. Little's FanFic's and Max part was written by Dark Spyr0.

* * *

Sydney could not believe it that she will be in Zach's house once again, and this time she is not babysitting his cute little brother Dylan. She thought looks must run in the family and Dylan one day will have girls all over him too just like his big brother Zach. Sydney was at the front door and she quickly fixed her hair as she wanted to look good for him. She was disappointed that she wasn't able to tell her friend Olive about being at the house because Zach did not want anyone else to know he needs help in history.

Sydney took a breath and rang the doorbell and waited. She was all nervous but can't wait to be with Zach. She only waited a minute, but that minute felt forever. When the door finally opened she saw it was Dylan on the other side. She was disappointed in hoping it was just Zach and herself. Dylan looked confused as he did not know he was going to be babysat today.

"Hi, Dylan is Zach here?"

"So you are not here to babysit me?"

"No, I don't think I am. Your brother just called me over for something and did not say anything about babysitting."

"Oh well, he's up in his room. It's across from mine if you remember where mine was."

Of course, I do sweety." Sydney cooed.

As Sydney made her way up the stairs she heard an odd noise and followed it. It got louder and saw a closed door. The room must be Zach's as Sydney could clearly look inside the room across from it was Dylan's. Sydney quietly knocked on the door but there was no answer. So she slowly opened the door and she dropped her book. This caused Zach to open his eyes and quickly cover himself up.

Zach was naked on his bed and sliding his huge dildo in and out of his ass. He was so into it he lost track of the time. Zach was not gay by all means but he was into ass play. Even if he only had played with his own ass. He did start with fingers a year ago but as he got a little older it wasn't enough and he used different things to use. As time went by the objects got bigger and longer. Now here he is covering up and a dildo up his ass.

* * *

Max was thrilled as he saw the girl he has been crushing on was more at the skatepark. He has been thinking as well as stroking himself to thoughts of her since he first saw her practicing her tricks five days ago. Since then he has learned her name Lexie due to overhearing her friends but still failed to have the confidence to approach and chat with her. He swore that he caught her watching him a few times as he rode his board and he fumbled his trick every time and ended up on the ground.

He was determined to impress her with his best move yet, he hadn't mastered it yet but he chose not to dwell on such a minor detail such as that because this was fate and he will successfully do it with her watching and will come running over demanding to be taught it and one thing will lead to another and soon he could smooch with her and get the guys all jealous as he got such an awesome girl and they have nobody or less amazing girlfriends.

Glancing over to see if she was watching he was dismayed to see that she wasn't raising his voice he pretended to chat with some guys that he really didn't know and they watched as he started his move. He was sure that Lexie also heard and was eager to see what he had in store for them.

He started going down the curve picking up speed than almost as fast started going up the side of the curve and was in the air, he moved to make the twists and turns he spent days practicing, Leo said he needed months but Max knew differently and his board slipped out of his hands and he felt himself falling and he felt himself his the ground and sliding to the boys laughter before meeting sweet darkness.

"Oh, where am I?" Max said to himself as he awoke in unfamiliar surroundings. His traitorous board was next to him to his delight.

"My room you jerk."

There was his future girlfriend with an angry expression on her face. Immediately he felt himself getting erect.

"Who are you calling me a jerk?" he asked bewildered.

"You are far too cute looking to get yourself beaten up trying to impress those boys."

"I wasn't trying to impress the boys!"

"Pul-leeze," said Lexie. "I heard you telling that friend of yours about befriending and joining those Dog Boys gang."

"They weren't the Dog Boys"

She scoffed. "Sure," she replied with even Max knowing she didn't believe him with the way she said it. "Anyway, I and my friends brought you here and treated your scrapes and bruises. Your Dog Boys friends or whoever you claim them to be in actuality did nothing but laughed and mocked you as you moaned." She actually liked the sounds he made while he moaned and twisted things inside her.

"Thanks," Max said. He now felt incredibly hard and he could smell her on her pillow he so badly wanted to steal the pillow and wank one out while smelling it. It didn't feel right to play with himself in her room.

This wasn't going the way he had hoped but he was in her room and they were alone and best of all they were talking. He wondered what to say, it needed to be something good and long term like teaching lessons as he wanted to entice her but that failed. As he wondered what to say he took in the room he was in and loved her all the more as it wasn't a girly room filled with stuff toys and pink walls.

She had posters of idols that even he favored and some he did not, a few he couldn't glance at for long as the boys featured were practically naked. She had a few boards hanging of her wall and medals from competitions. He knew with an illogical logic that he himself would have some too if he knew of the competition earlier, as the deadline has passed or had better luck during tryouts.

Her room was a mess and that pleased him to no end as he knew if they survived the coming years she won't be the nagging wife asking him to clean up his side of the room or trying to change him. All the while Lexie watched him and her brows furrowed when she saw he took no delight in perving on the semi-naked guys.

"What's wrong? They not to your taste?" she asked him.

"Huh?"

She walked and Max followed her with his eyes as she approached a pic that made Max blushed as the older teen was practically naked with his chest exposed and his pants hanging loosely from his waist showing off the underwear he wore.

"Is he not your type?" she asked.

"Of course not, he's a boy!"

"But your gay aren't you?"

"I am not gay!"

"You don't have to deny it. My uncle is gay and I know one of my cousins is and I even have a friend who's gay. So you can tell me if you want."

"I... AM... NOT... GAY." Each word was said slowly as if to emphasize his point nor was it yelled but said clearly.

"Are you sure? I mean you didn't bat an eye when I called you cute earlier and you are always hanging around that black friend of yours and let's not return to those Dog Boys you are constantly raving about."

Max stopped listening when he heard her calling him cute. He didn't even pick up that she must have been paying him more attention then he knew to jump to the wrong conclusion of him.

"You think I'm cute?"

It was now her turn to blush and before he knew it without saying a word she turned and left her room slamming the door behind her.

That could have gone better. Max thought dismayed he was seriously hoping for a kiss and perhaps a punch on the shoulder afterward calling him a fool for not realizing it earlier.

He toyed with following after her but his boner was annoying him and he didn't want to seek her out with tented shorts, he also still felt awkward doing it in her room. Deciding to free his erection and give it a few tugs before returning it in the confines of his underwear in a more comfortable position he lifted his ass of her sheets and pulled down both his pants and underwear.

A little later he regretted his stupidity as he was still hard and no position he tried help. He also thought to do a little snooping before she returned or his predicament was less obvious so he could look for her without looking like a horny fool. As for the snooping, he saw it was within his right as the two of them would soon be a couple and he needed to know her better.

He still was faring well and stayed near the bed so not a lot of time has passed since Lexi left him. The nearby drawers were unlocked till he hit one that was.

Surely the key would be nearby! Max thought.

He looked for the key unaware that his boner now with Lexi gone and his mind fixated on the locked drawer, was a semi and deflating quickly.

He lifted up the bedside lamp and found a key. Placing it inside the lock he turned it and tried opening it. Inside he was shocked to discover condoms, unopened, a dildo, something that looked like underwear that wouldn't be functional as it would covered nothing, handcuffs, something that might be a whip but he wasn't sure if it was or not as it was small and had several ends instead of the traditional one, a paddle, rope and to Max's delight poems and while he had a big head he was right in his assumption that they were about him.

Some of the poems featured him as straight but most had him down as gay and she wrote how amazing it would be to see him getting it up the ass, gagging on a boy's prick, getting spanked for being a whore and even getting rimmed. While this would have him he was in fact excited to read on just how much his girl obsesses over him. The two of them were so much alike, as Max never even entertain being with another girl since laying eyes on her.

His boner was now on full mast and Max wanting to read each and everyone played with himself unconsciously as he flipped through the many pages. He never even heard Lexi returning apologizing for her rude behavior while holding a tray of food for them to share.


	2. Chapter 2

**Disclaimer**

Neither one of us has any rights to Sydney to the Max. We have not met the actors nor privy to their sexuality. We do own this story.

**Author Note**

Sydney part is written by L. Little's FanFic's and Max part was written by Dark Spyr0.

_Previously_

_Zack was naked on his bed and sliding his huge dildo in and out of his ass. He was so into it he lost track of the time. Zack was not gay by all means but he was into ass play. Even if he only had played with his own ass. He did start with fingers a year ago but as he got a little older it wasn't enough and he used different things to use. As time went by the objects got bigger and longer. Now here he is covering up and a dildo up his ass._

**_And_ _Now__..._**

"Please don't tell anyone about this."

"Yah um ok, so you are gay then?"

"Well no I just like ass play is all."

"So you play with other people's asses?"

"No just mine."

"Well ok do you want to get dressed and start what I came for?"

"Yeah but um could you, you know leave the room?"

"I already saw you naked. Even if it was short lived."

"Well I guess you can watch me get changed."

By now Zach's dick was now soft and his dildo slid out of his ass. He was not thinking straight when he pulled open the wrong draw. There Sydney saw other sex toys and one of them looked strange. Out of instincts she picked up the cage looking item. Zach eyes widen on his mistake and then seen what was in Sydney's hand.

"What's this?"

Zach quickly took the thing out of her hand and put it into the draw then closed it before he turned around with his back against the dresser.

"You doing that did not answer my question. I could rat you out you know."

Fine. It's well a cage for my dick."

"why?"

"Well it looked interesting so I bought it."

"But what does it do?"

"It goes around my dick and provents me from masterbating. Normally its a slave master kind of thing. This one just happens to have a hole at both ends so I can go to the washroom if I keep it on not during master slave time. The master is in control of the cage and holds on to the key. Of course there is a spare just incase the master loses the key."

"Interesting. Can I see it on you?"

"Are you asking just to see it on for curiosity sake or you considering being my master and that was supposed to be an order?"

"Well what does the master do? This is all new to me."

"I'm a strong believer in femdom. If I expect you to take it up the ass shouldn't it be right for a guy to offer his ass in return. If I want you to deepthroat my cock and possibly gag on it, then shouldn't I be open to doing the same? But that's just my opinion."

Sydney found herself nodding to his comments but was confused by them at the same time. Girls cant fuck a guy or get deepthroated so his words were hollow weren't they?

She decided to ask, and did so as Zach didn't seem the type to get angry with being questioned.

"So how can a girl do those things to a guy when they don't have a dick?"

"Well using a dildo for one or a strap on."

"A what now?"

"A strap on it's like a belt with a dildlo attached to it. The dildo part is the thing you saw me use on my ass."

"So what does a girl have to do to you to see that cage thing on your dick?"

Sydney taking a risk and placed her hand on his soft dick but did not know what to do with it. His dick quickly became hard in her hand. Sydney was amazed how a dick feels in her hand and wondered if all dicks feel the same and even look the same. Since this was her first time seeing a boy's dick. Zach smiled and placed his hand on top of hers that was on his dick and helped her jack him off.

Zach leaned in as he continued to help Syndey jack off as his other hand was on the back of her head. The two soon had their first kiss. The kiss was a small one but Sydney wanted more with her other hand she pulled Zach back into the kiss. Something woke up inside her that day. She guided him back to his bed and before they realized it Zach was on his back with Sydney on top of him.

* * *

_Previously_

_His boner was now on full mast and Max wanting to read each and everyone played with himself unconsciously as he flipped through the many pages. He never even heard Lexi returning apologizing for her rude behavior while holding a tray of food for them to share._

**_And__Now__..._**

She was furious watching him read her poems, they weren't any good she thought but she enjoyed writing her fantasies in such a manner the challenge thrilled her but no one was ever meant to read how turned on she was by him or how wet and horny she felt imagining him doing such nasty things with other boys, that was of course after she started thinking he was gay.

Max heard the tray and food hitting the ground and turned around with alarm with one hand still down his pants holding himself while the other held the latest poem the rest laid on top of her drawer awaiting him to choose another to read.

"LEXI!" he unintentionally yelled.

"Cute jerk," she replied with venom. She never did learn his name.

"I... uh… well… what are you doing here?"

"I live here, and you are leaving. I can't believe you were reading my private stuff!" She grabbed him by the ear and started leading him out. He limped after her, partly by being led by the ear as well as his latest burnout.

"Lexi I'm sorry, I just wanted to know you a bit better, I didn't know it was private!"

"IT... WAS... LOCKED!" It wasn't yelled but emphasized as Max did earlier.

"Sorry," Max said meekly. "Then hurriedly as he thought they were approaching the front door. "Please don't throw me out, I think your awesome on the board as well as off and you're stunning, you're a real hot babe that any guy would be lucky enough to call you his girl and… and… please, I do anything to make it up to you." He almost felt as if he would be sobbing at any moment.

His experience since waking up in her room threw him through a loop and he wasn't sure if it was his injury or being around her, or even his own mental capabilities but clearly he missed one or more signs that she gave out that should have alerted him that she was keen on him, or at least that she used to be as he thought that if he passed through her threshold he would never be her boyfriend.

"Please,"

She stopped and let go of his ear and Max dropped to the ground in relief as he couldn't support his own weight. He fought down tears and the need to sob as that wouldn't be manly.

"I still wonder if you are straight or not so…" she trailed off as she continued to ponder her line of thought.

Ouch, Max thought. Do I really talk about the Dog Boys that much that she thought I was crushing on the lot of them!

"Convince me," she said after staring down at him as he sat on his ass with his feet outstretch as comfortable as he could get them.

"Convince you how? About what? That I'm straight?"

"That you are sorry and that you are straight. I want to see you cum without touching yourself by pleasuring me with your mouth."

Max gulped in alarm, he dreamt of this but he didn't expect this before a month or more of dating and he wasn't allowed to use his hands. He feared that without actual intercourse or hands that he would fail and forever be labeled as gay by her.

"Lexi, I-" Max attempted to tell her about his fears of her plan.

"Goddess Lexi, Mistress or Queen Lexi, jerk. You are begging forgiveness for invading my privacy after all so you have no right by simply calling me by my name."

"My name is Max," Max said with a smile extending his arm for her to shake, or to assist him with standing up.

"And at this moment I don't care," Lexi said while staring at him. She pictured him naked and like what her imagination cooked up.

Pouting Max got up all wobbly and leaning against the wall for support as he waited to see how she wanted him to cum by just using his mouth to pleasure her.

Was such a thing even possible_?_

"Let's return to my room," Lexi said watching him with some concern. Still, she did not assist him as she didn't want Max to see how much she cared.

Using the wall Max followed her slowly while staring at her ass. He did nothing to hide his smile when she caught him staring. She closed the door after him.

"I want you to strip down to your underwear and I will be placing these on you." She walked over to the drawer he violated and removed the handcuffs. "Behind your back of course, so you won't pleasure yourself while kissing me, sucking my breasts or eating me out. There won't be any actual fucking as you might pretend I'm a boy getting it up the ass."

"Lexi, I'm not-"

Lexi slapped him on the cheek. She wasn't going for pain or leaving a mark it was more for shock value than anything.

"Queen, Goddess or Mistress." Lexi reminded him

"Goddess Lexi, I really am not gay so this…" he trailed off seeing her angry expression.

"Why are you still dress? I want to see you naked before me." She smiled and Max liked the smile as he felt it was due to him, which it was. She always wanted to see him nude before and even after when she thought she had no chance with him and already she thought of a way to have him return after his punishment with a gift her cousin gave to her surprisingly enough that very day. It laid in her bag and wasn't placed in her drawer as she didn't have the time to put it in its new home.

Excited and nervous Max sat down and stripped. He still did not feel strong enough to stand and his nerves didn't help matters. He was nervous as he has never been seen naked by a beautiful girl and Lexi was hot. She was a little taller then he and her hair was a dark black and long tied back in a ponytail. She has a healthy tan and her eyes that Max was afraid to look at as he feared he would get lost in them, he heard that could happen, avoided staring as he didn't want to be caught by her or teased by his friends, knew them to be a good mix of blue and green. He thinks of them as eyes that reflect the seas.

She had bruises and cuts, a few bandages that don't remain on for long with her skateboarding. He never knew her to wear dresses and Max approves nor did he believe she wore makeup as she didn't need them. But he would learn later that she did. Overall from what she told him he will see her naked so he could bury his face in her chest and lick at her opening and he couldn't wait so that was why he was excited.

"Not bad, not bad at all," Lexi said when he was nude from the waist up.

Her feet went up to Max's bare chest and applied just enough pressure to topple him onto his back. Her shoe carefully moved up and down his chest, and she stopped as it presses gently against his hidden wood.

"Now show me your goods,"

Still nervous and strangely turned on Max started unfastening the strings that held up his shorts and once her foot left rose his ass off the floor pulling down both his shorts and underwear. He was red in the face and it wasn't due to his injury.

Lexi whistled in appreciation and Max couldn't help himself but look away in embarrassment. He turned back when he heard Lexi say that it was now her turn.


End file.
